Dimethylformamide → Methyl 3-methoxy-5-(methylsulfonyl)benzoate

HRID 1373105Notes

Reaction equation

HRID 1373105 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:10]=1)[C:5](O)=[O:6].[C:15](=O)([O-])[O-].[Cs+].[Cs+].CI.CN([CH:26]=[O:27])C>>[CH3:15][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:10]=1)[C:5]([O:27][CH3:26])=[O:6]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 210741973-Hydroxy-5-methylsulfonylbenzoic acid

Product 1

HCID 21074200Methyl 3-methoxy-5-(methylsulfonyl)benzoate

Procedure

3-Hydroxy-5-methylsulfonylbenzoic acid (D13) was dissolved in DMF (42 ml) and treated with caesium carbonate (14.1 g) and methyl iodide (8.6 ml) The mixture was sonicated under argon for 45 min. and stirred for 3 h at room temperature. The DMF was evaporated in vacuo and the residue was partitioned between ethyl acetate and 2M hydrochloric acid. The aqueous layer was re-extracted twice with ethyl acetate and the combined extracts were washed with sodium bicarbonate solution, sodium thiosulfate solution, water and brine, dried (Mg SO4) and evaporated to a semi solid. Trituration with ether gave D14 (2 crops, 2.94 g).

Workup

  1. customwas sonicated under argon for 45 min.
  2. customThe DMF was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate and 2M hydrochloric acid
  4. extractionThe aqueous layer was re-extracted twice with ethyl acetate
  5. washthe combined extracts were washed with sodium bicarbonate solution, sodium thiosulfate solution, water and brine
  6. dry with materialdried (Mg SO4)
  7. customevaporated to a semi solid
  8. customTrituration with ether gave D14 (2 crops, 2.94 g)

Sources & evidence

ORD record
ord-a6e405a677b14ea6a4516204ee0aadd3
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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